Midomafetamine

Summary

Midomafetamine (CHEMBL43048) is a phase-3 clinical-stage small molecule; indicated across 13 conditions including post-traumatic stress disorder and anxiety.

At a glance

• Status: Max clinical phase 3 (not approved)
• Modality: Small molecule
• Indications: 13 conditions
• Clinical trials: 84
• Chemistry: 193.24 Da · C11H15NO2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL43048
Name	Midomafetamine
Type	Small molecule
Max phase	3
FDA approved	no
PubChem CID	1615
ChEBI	CHEBI:1391
Molecular formula	C11H15NO2
Molecular weight	193.24
InChIKey	SHXWCVYOXRDMCX-UHFFFAOYSA-N

SMILES: CC(CC1=CC2=C(C=C1)OCO2)NC

IUPAC name: 1-(1,3-benzodioxol-5-yl)-N-methylpropan-2-amine

ChEBI definition: A member of the class of benzodioxoles that is 1,3-benzodioxole substituted by a 2-(methylamino)propyl group at position 5.

Pharmacological roles (ChEBI): neurotoxin.

Also known as: Ecstasy, Mandy, Mdma, Methylenedioxymetamphetamine, Methylenedioxymethamfetamine, Methylenedioxymethamphetamine, Midomafetamina, Midomafetamine, Molly, Methylenedioxy methamphetamine, methylenedioxymethamphetamine, Methylenedioxy methamphetamine (MDMA)

Parent form; salt/anhydrous children: CHEMBL3189075

Patent coverage: 2,697 distinct patent families (7,261 SureChEMBL compound mentions), from 2 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 8 (assay-derived). Sample: Neuronal acetylcholine receptor; alpha4/beta2, Sodium-dependent noradrenaline transporter, Sodium-dependent serotonin transporter, Sodium-dependent dopamine transporter, Cytochrome P450 2D6, Sodium-dependent serotonin transporter, Sodium-dependent dopamine transporter, Trace amine-associated receptor 1.

Bioactivity

ChEMBL activities: 25 potent at pChembl ≥ 5 of 29 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
SLC6A4	9.14	Ki	0.73	nM	CHEMBL_ACT_2348888
SLC6A4	8.69	Ki	2.03	nM	CHEMBL_ACT_2348896
P31652	7.21	EC50	61	nM	CHEMBL_ACT_15674902
P31652	7.14	EC50	72	nM	CHEMBL_ACT_18042082
P23977	7.12	EC50	75	nM	CHEMBL_ACT_15674901
P23977	6.56	EC50	278	nM	CHEMBL_ACT_18042095
SLC6A2	6.4	Ki	398	nM	CHEMBL_ACT_13336340
SLC6A2	6.39	IC50	405	nM	CHEMBL_ACT_3217881
SLC6A2	6.39	IC50	405	nM	CHEMBL_ACT_3344075
SLC6A4	6.37	IC50	425	nM	CHEMBL_ACT_3217876
SLC6A4	6.37	IC50	425	nM	CHEMBL_ACT_3344074
SLC6A3	6.05	Ki	897	nM	CHEMBL_ACT_13336360
SLC6A4	6.02	Ki	948	nM	CHEMBL_ACT_13336320
SLC6A2	6	EC50	1000	nM	CHEMBL_ACT_15674894
SLC6A3	6	EC50	1000	nM	CHEMBL_ACT_15674895
SLC6A4	6	EC50	1000	nM	CHEMBL_ACT_15674896
P31652	5.97	IC50	1060	nM	CHEMBL_ACT_3216572
SLC6A4	5.96	IC50	1100	nM	CHEMBL_ACT_5219265
P09483	5.84	Ki	1440	nM	CHEMBL_ACT_14670604
SLC6A3	5.84	IC50	1442	nM	CHEMBL_ACT_3217885
SLC6A3	5.84	IC50	1442	nM	CHEMBL_ACT_3344076
Q923Y9	5.77	EC50	1700	nM	CHEMBL_ACT_7968706
SLC6A2	5.7	IC50	1995	nM	CHEMBL_ACT_13336341
SLC6A3	5.62	IC50	2399	nM	CHEMBL_ACT_13336361
SLC6A4	5.56	IC50	2754	nM	CHEMBL_ACT_13336321

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

13 indications (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
post-traumatic stress disorder	3	MONDO:0005146	EFO:0001358
anxiety	2	MONDO:0011918	EFO:0005230
social phobia	2	MONDO:0001247	EFO:1001917
anorexia nervosa	2	MONDO:0005351	MONDO:0005351
eating disorder	2	MONDO:0005451	EFO:0005203
drug dependence	1	MONDO:0005303	EFO:0003890
liver disorder	1	MONDO:0005154	EFO:0001421
methamphetamine dependence	1	MONDO:0005419	EFO:0004701
alcohol abuse	1	MONDO:0002046	MONDO:0007079
autism spectrum disorder	0	MONDO:0005258	EFO:0003756
fibromyalgia	0	MONDO:0005546	EFO:0005687

2 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 84.

Phase distribution

Phase	Trials
PHASE2	30
PHASE1	28
EARLY_PHASE1	9
Not specified	9
PHASE3	5
PHASE1/PHASE2	3

Top trials by phase / activity

NCT	Phase	Status	Title
NCT03537014	PHASE3	COMPLETED	A Multi-Site Phase 3 Study of MDMA-Assisted Psychotherapy for PTSD (MAPP1)
NCT04077437	PHASE3	COMPLETED	A Multi-Site Phase 3 Study of MDMA-Assisted Psychotherapy for PTSD (MAPP2)
NCT04714359	PHASE3	COMPLETED	A Multi-Site Open-Label Extension Study of MDMA-Assisted Psychotherapy for PTSD
NCT05979844	PHASE3	COMPLETED	MDMA-assisted Brief Cognitive Behavioral Conjoint Therapy for PTSD
NCT06189027	PHASE3	COMPLETED	Epigenetics and MDMA-Assisted Psychotherapy for PTSD
NCT05455996	PHASE2	NOT_YET_RECRUITING	MDMA-Assisted Therapy for Stress Disorders in Healthcare Workers and First Responders
NCT05584826	PHASE2	RECRUITING	MDMA-assisted Therapy for Adjustment Disorder (AD) in Dyads of Patients With Cancer and a Concerned Significant Other
NCT05709353	PHASE2	RECRUITING	MDMA-assisted Prolonged Exposure Therapy for Comorbid Alcohol Use Disorder and Post-traumatic Stress Disorder
NCT05746572	PHASE2	ENROLLING_BY_INVITATION	MDMA Plus Exposure Therapy for PTSD
NCT05770375	PHASE1/PHASE2	RECRUITING	Tolerability of MDMA in Schizophrenia
NCT05790239	PHASE2	RECRUITING	MDMA-Assisted Therapy for Veterans With Moderate to Severe Post Traumatic Stress Disorder
NCT05837845	PHASE2	RECRUITING	MDMA-assisted Cognitive Processing Therapy Versus Cognitive Processing Therapy for Veterans With Severe Posttraumatic Stress Disorder
NCT05943665	PHASE2	RECRUITING	MDMA for AUD/PTSD Comorbidity
NCT06418178	PHASE2	RECRUITING	Dose Optimization of MDMA-Assisted Therapy for PTSD
NCT06683014	PHASE2	RECRUITING	MDMA in Borderline Personality Disorder
NCT07288151	PHASE2	RECRUITING	MDMA-Assisted Massed Exposure Therapy for PTSD
NCT07301632	PHASE2	RECRUITING	Ecstasy to Alleviate SEvere Chronic Neuropathic Pain Trial
NCT07569159	PHASE2	NOT_YET_RECRUITING	MDMA Therapy in Veterans With PTSD
NCT00090064	PHASE2	COMPLETED	MDMA-Assisted Psychotherapy in People With Posttraumatic Stress Disorder
NCT00353938	PHASE2	COMPLETED	Study of 3,4-Methylenedioxymethamphetamine-assisted Psychotherapy in People With Posttraumatic Stress Disorder
NCT01458327	PHASE2	COMPLETED	Additional MDMA-assisted Therapy for People Who Relapsed After MDMA-assisted Therapy Trial
NCT01958593	PHASE2	TERMINATED	Randomized, Double-blind, Controlled of MDMA-assisted Psychotherapy in 12 Subjects With PTSD
NCT02008396	PHASE2	COMPLETED	Phase 2 Pilot Safety Study of MDMA-assisted Therapy for Social Anxiety in Autistic Adults
NCT02427568	PHASE2	COMPLETED	MDMA-Assisted Psychotherapy for Anxiety Associated With a Life-Threatening Illness
NCT02876172	PHASE1/PHASE2	COMPLETED	MDMA-Assisted Cognitive-Behavioral Conjoint Therapy (CBCT) in Dyads in Which 1 Member Has Chronic PTSD
NCT03282123	PHASE2	COMPLETED	Open Label Multi-Site Study of Safety and Effects of MDMA-assisted Therapy for Treatment of PTSD
NCT03485287	PHASE2	COMPLETED	Study of Safety and Effects of MDMA-assisted Psychotherapy for Treatment of PTSD (Canada)
NCT04030169	PHASE2	COMPLETED	Open Label Study of MDMA-assisted Psychotherapy for Treatment of PTSD With Optional fMRI Sub-Study
NCT04264026	PHASE2	COMPLETED	MDMA-Assisted Psychotherapy in Veterans With Combat-Related, Refractory PTSD
NCT04454684	PHASE2	WITHDRAWN	A Multi-Site Study of MDMA-Assisted Psychotherapy for Eating Disorders
NCT04784143	PHASE2	TERMINATED	Study Comparing Two Versus Three Active MDMA-assisted Sessions in U.S. Military Veterans With Chronic PTSD
NCT04968938	PHASE2	WITHDRAWN	Study of Safety and Effects of MDMA-assisted Therapy for Treatment of PTSD
NCT05067244	PHASE2	COMPLETED	A Phase 2 Open-Label Treatment Development Study of MDMA-Assisted Cognitive Processing Therapy (CPT) for Posttraumatic Stress Disorder (PTSD)
NCT05138068	PHASE2	COMPLETED	Social Anxiety MDMA-Assisted Therapy Investigation
NCT05173831	PHASE2	WITHDRAWN	Study of Feasibility and Safety of MDMA-Assisted Group Therapy for the Treatment of PTSD in Veterans
NCT05732155	PHASE2	UNKNOWN	Preliminary Effectiveness of Individual and Group MDMA-assisted Therapy for Israeli Veterans With PTSD and Moral Injury.
NCT05961527	PHASE1/PHASE2	COMPLETED	Group MDMA-therapy for Veterans With PTSD
NCT06353282	PHASE2	WITHDRAWN	MDMA-Assisted Psychotherapy for Treatment Resistant PTSD in Adolescents
NCT03606538	PHASE1	NOT_YET_RECRUITING	MDMA in Subjects With Moderate Hepatic Impairment and Subjects With Normal Hepatic Function
NCT06772753	PHASE1	RECRUITING	Investigation of Psychedelic Effects in Psychoactive Substances

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 6 clinical and 12 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).